How a daily challenge can change your life.


[This email was originally sent Tuesday, Jan 6th but a link was mistakenly flagged as spam causing it to land in most people's junk inbox. Sorry for the inconvenience.]

In June of 2023 I was bored.

It had been two months since I quit drinking and I was restless. What do sober people do for fun? I couldn't remember.

I tried hiking on the weekends with friends to reclaim that sense of adventure I was missing. During these hikes I would take photos with my phone and eventually had the idea to buy a digital camera to document these excursions. I acted on impulse and bought a brand new camera that I had no clue how to use.

I decided the best way to figure out this photography thing was to immerse myself in a 365-day challenge (In hindsight, a bit over-zealous). Every day I would shoot, edit, and then post a photo based on a one-word prompt I grabbed from an old photography blog site.

Each day became an adventure. My camera went with me everywhere: dog walks, cafe shops, hiking trails, beach trips, dinner parties, and work. I wanted to make it as easy and obvious as possible to take a photo when the right moment revealed itself. My morning walks with my dog got longer and more varied. My wife and I explored more of the city. I even made new friends with like-minded photographers.

I started telling coworkers about the challenge which meant people started to follow along to see my posts. Suddenly, I felt accountable to someone outside of myself. I knew nobody would care or even notice if I missed a day, but I would know. I felt responsible to show up.

Eventually people started to ask me how I did it. "How do you stay so consistent day after day?" I thought if people were curious maybe I should write about it and so I did. I started publishing articles on Medium writing how-to's and habit guides. Now I felt accountable as a writer to my tiny cohort of readers.

Around the 100-day mark I wanted to quit. I realized that I was more passionate about writing than taking photos. Photography got me outside learning new things and exploring more of life but it wasn't what I wanted to pursue with the rest of my life.

But I didn't quit after 100 days. Instead, I added writing to my daily challenge. and continued doing both until I reached day 247.

I only quit after realizing I got what I needed from the challenge. I learned how to build a new habit and overcome daily obstacles. I learned how to set goals, deadlines, and create accountability systems. I learned how to stick with something even on days that I didn't feel like it. Most importantly, I learned that I didn't need inspiration or grand ideas to create; I just needed to show up every day.

More than nine-hundred days later I'm still sober and still writing.

I've since done many more daily challenges and experiments:

  • Bullet journaling for 30 days turned into 9 months and counting.
  • I tried a 30-day drawing challenge that led me to explore relief printing.
  • A 15-minute daily reading challenge turned into an hour or more a day over time.

Consistency is a skill. A daily challenge is a great vehicle for learning those skills. You will learn how your inner demons try to convince you to skip a day. You will learn when it's time to push past a wall or call it quits. You will learn everything you need to know to become consistent by acting consistently.

You might end up somewhere unexpected like I did but you will have learned something about yourself along the way.

All you've got to do is start.


Prompt:

When was a time you committed to a challenge? What did you learn about building habits? What did you learn about yourself?

If journaling every day is a habit you want to commit to then I highly recommend this video I made where I take the principles of Atomic Habits by James Clear and apply them specifically to building a journaling habit.

video preview

The Creator Cycle

Self-mastery with pen-and-paper systems.

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